21.11.7 Chemoselective Ligation Methods Based on the Concept of Native Chemical Ligation

2021 ◽  
Author(s):  
L. R. Malins ◽  
R. J. Payne
Keyword(s):  
Peptide Synthesis ◽  
Native Chemical Ligation ◽  
Chemical Ligation ◽  
Chemoselective Ligation ◽  
Ligation Reaction ◽  
Recent Developments ◽  
Peptide Ligation

AbstractThis chapter extends from the earlier Science of Synthesis contribution on peptide synthesis (Section 21.11) and focuses on recent developments in chemoselective ligation chemistry based on the logic of native chemical ligation. Synthetic strategies that broaden the scope and versatility of the ligation reaction and that have been widely adopted for the preparation of homogeneous peptides and proteins are highlighted. Methods enabling the efficient preparation of peptide ligation precursors are also included in this chapter.

One-pot native chemical ligation by combination of two orthogonal thioester precursors

2017 ◽  
Vol 53 (13) ◽  
pp. 2114-2117 ◽  
Author(s):  
Yuya Asahina ◽  
Toru Kawakami ◽  
Hironobu Hojo
Keyword(s):  
Native Chemical Ligation ◽  
Protecting Group ◽  
One Pot ◽  
Chemical Ligation ◽  
Ligation Reaction ◽  
Ligation Method ◽  
Peptide Ligation

We developed a one-pot peptide ligation method using two orthogonal thioester precursors and a protecting group for the ligation reaction between Asp and Cys.

scholarly journals Reinvestigation of a Critical Reductive Amination Step Leads to an Optimized Protocol for the Synthesis of N-2-Hydroxybenzylcysteine Peptide Crypto-Thioesters

2020 ◽  
Author(s):  
Skander Abboud ◽  
Vincent AUCAGNE
Keyword(s):  
Peptide Synthesis ◽  
Reaction Mechanisms ◽  
Reductive Amination ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Building Blocks ◽  
Native Chemical Ligation ◽  
Chemical Ligation ◽  
Optimized Protocol ◽  
Depth Study

An in-depth study of the Fmoc-based solid phase peptide synthesis of N-Hnb-Cys crypto-thioester peptides, advantageous building blocks for the native chemical ligation-based synthesis of proteins, led to the identification of epimerized and imidazolidinone side products formed during a key reductive amination step. The understanding of the underlying reaction mechanisms was crucial for the developement of an automatable optimized synthetic protocol.

scholarly journals Serine promoted synthesis of peptide thioester-precursor on solid support for native chemical ligation

2017 ◽  
Vol 8 (1) ◽  
pp. 117-123 ◽  
Author(s):  
Hader E. Elashal ◽  
Yonnette E. Sim ◽  
Monika Raj
Keyword(s):  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Solid Support ◽  
Native Chemical Ligation ◽  
Selective Activation ◽  
Chemical Ligation ◽  
Peptide Thioester ◽  
Peptide Thioesters

Fmoc solid phase peptide synthesis of peptide thioesters by displacement of the cyclic urethane moiety obtained by the selective activation of C-terminal serine.

scholarly journals Thiazolidine Deprotection by 2-Aminobenzamide-Based Aldehyde Scavenger for One-Pot Multiple Peptide Ligation

2021 ◽  
Author(s):  
Koki Nakatsu ◽  
Hitoshi Murakami ◽  
Gosuke Hayashi ◽  
Akimitsu Okamoto
Keyword(s):  
Native Chemical Ligation ◽  
High Yield ◽  
Side Reactions ◽  
Model Peptide ◽  
One Pot ◽  
Chemical Ligation ◽  
Good Ability ◽  
Synthetic Proteins ◽  
Short Time ◽  
Peptide Ligation

Strategies for one-pot peptide ligation enable chemists to access synthetic proteins at a high yield in a short time. Herein, we report a new one-pot multi-segments ligation strategy using N-terminal thiazolidine (Thz) peptide and a formaldehyde scavenger. Among our designed 2-aminobenzamide-based aldehyde scavengers, 2-amino-5-methoxy-N’,N’-dimethylbenzohydrazide showed a good ability to capture formaldehyde from Thz at pH 4.0. This scavenger had compatibility with the conditions of native chemical ligation at pH 7.5. Using this scavenger for a model peptide ligation system, we performed one-pot four-segment ligation at a high yield without significant side reactions.

Cover Picture: Expanded Utility of the Native Chemical Ligation Reaction (Chem. Eur. J. 19/2004)

2004 ◽  
Vol 10 (19) ◽  
pp. 4651-4651
Author(s):  
Dawn S. Y. Yeo ◽  
Rajavel Srinivasan ◽  
Grace Y. J. Chen ◽  
Shao Q. Yao
Keyword(s):  
Native Chemical Ligation ◽  
Chemical Ligation ◽  
Ligation Reaction
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